Total Synthesis of Bioactive Natural Products by Palladium-Catalyzed Domino Cyclization of Allenes and Related Compounds
Authors: Inuki, Shinsuke
Free Preview- Total synthesis of the bioactive natural products, pachastrissamine, lysergic acid, lysergol and isolysergol, by palladium-catalyzed domino cyclization of allenes and related compounds is investigated
- Gives an insight to the development of efficient synthetic approaches for biologically active compounds
- Nominated as an oustanding contribution by Kyoto University
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- About this book
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The author has developed novel methodologies for highly efficient construction of functionalized heterocycles by palladium-catalyzed domino/cascade cyclization of allenes and related compounds containing appropriate nucleophilic group(s). Based on these methodologies, enantioselective total syntheses of bioactive natural products, pachastrissamine (26% overall yield in seven steps), lysergic acid (4.0% overall yield in fifteen steps), lysergol (3.6% overall yield in fifteen steps) and isolysergol (8.2% overall yield in eleven steps) have been achieved. These are more facile synthetic route than those previously reported. These findings would contribute to the development of efficient synthetic methods for biologically active compounds containing a complex structure.
- Reviews
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From the reviews:
“The target audience … includes practicing organic chemists with interests in synthesis, and those with specific interests in palladium-catalysed organic reactions, and as such is suited to graduate level and above. … is well-written and provides plenty of food for thought for specialists in palladium(II) chemistry … . the book also benefits from a comprehensive experimental section at the end of each chapter. … the book reflects the high quality experimental skills of the author, and provides a useful handbook for the synthetic organometallic chemist.” (Edward A. Anderson, Platinum Metals Review, Vol. 56 (3), 2012)
- Table of contents (6 chapters)
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Introduction
Pages 1-8
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Total Synthesis through Palladium-Catalyzed Bis-Cyclization of Bromoallenes
Pages 11-27
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Total Synthesis through Palladium-Catalyzed Bis-Cyclization of Propargyl Chlorides and Carbonates
Pages 29-49
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Palladium-Catalyzed Domino Cyclization of Amino Allenes Bearing a Bromoindolyl Group and Its Application to Total Synthesis of Ergot Alkaloids
Pages 53-75
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Total Synthesis of (+)-Lysergic Acid, (+)-Lysergol, and (+)-Isolysergol
Pages 77-103
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Table of contents (6 chapters)
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Bibliographic Information
- Bibliographic Information
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- Book Title
- Total Synthesis of Bioactive Natural Products by Palladium-Catalyzed Domino Cyclization of Allenes and Related Compounds
- Authors
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- Shinsuke Inuki
- Series Title
- Springer Theses
- Copyright
- 2012
- Publisher
- Springer Japan
- Copyright Holder
- Springer
- eBook ISBN
- 978-4-431-54043-4
- DOI
- 10.1007/978-4-431-54043-4
- Hardcover ISBN
- 978-4-431-54042-7
- Softcover ISBN
- 978-4-431-56110-1
- Series ISSN
- 2190-5053
- Edition Number
- 1
- Number of Pages
- XVI, 106
- Topics
